One filly, Lady Navarre, had finished second in the Kentucky Derby in 1906. In 1915, Regret carried the female banner to the winner's circle for the first time.
Regret not only won the 1915 Kentucky Derby as the first female victor, she helped popularize it and put sentiment in motion that referred to the race as the greatest thoroughbred race in America. Such was the winning remark of her owner, Harry Payne Whitney.
Economic problems plagued Churchill Downs by 1902, after Louisville and the Downs had thrived in the mid-1980s. Businessman Colonel Matt Winn accepted the challenge to rejuvenate the Derby economically.
Although Donerail's winning of the classic in 1913 that produced a large mutuel betting payoff ($184.90 for two dollars), and Old Rosebud boosted the Kentucky event in 1914 by winning it as the nation's premier thoroughbred, it was the filly Regret's effort in 1915 that put permanent frosting on the slightly fallen cake.
James Rowe was the Whitney filly's trainer. His expertise was well known and avidly sought. In his time, he trained 34 champions. Regret was sired by Broomstick from Jersey Lightning, a daughter of Hamburg, and foaled at Brookdale Farm, New Jersey. Jersey Lightning had plenty of winning tested blood in her lineage.
Regret blitzed through a juvenile campaign of fourteen days at Saratoga, racing in the Saratoga Special, the Sanford Stakes, and the Hopeful Stakes with top weight and beating the boys. Rowe believed a race horse was worthy if he could withstand his training regimen.
Rowe brought the filly with the pretty white, wide blaze to Kentucky at peak physical condition. Colonel Winn had public anticipation at its peak, having attracted the top Eastern bloodstock owners to the Derby. Rowe's regal, unbeaten chestnut filly lured the public twice in breezing workouts the full length of the impending Derby.
Joe Notter, former jockey of Colin, was in Regret's saddle, as usual, and Regret's chief juvenile rival, Pebbles, was on hand to entice the betting. Regret had beaten Pebbles twice at higher weight by short margins. On Derby day, all sported weights from 110 to 117 pounds. Regret carried 112, fifteen pounds less than on her last occasion with Pebbles.
In the previous three seasons, fillies had run to third place finishes in the Derby. Lady Navarre had run second in 1906. While no filly before Regret had won the classic, there was female participation precedence, a shortened distance (to 1-1/4 miles from the 1800's 1-1/2 miles), and Regret's juvenile experience running against colts.
There was reason to make her the favorite by 5-2.
On the negative side, there had been rumors that Regret hadn't traveled well from New Jersey to Kentucky and was, in fact, off her best game.
In the end, it was all speculative race day chatter.
Notter and Regret jetted to the front when the race finally got under way and easily turned back Pebbles in the final five furlongs, while Sharpshooter got to third. The filly shaved off two seconds of Old Rosebud's track and stakes record, winning in 2:05-2/5.
The filly was triumphant, and the Kentucky Derby was back on top as America's premier thoroughbred showcase.